ZipRecruiter

Log In

1

Insurance Transformation Jobs in Pennsylvania (NOW HIRING)

Deloitte

Guidewire PolicyCenter Sr Developer

Philadelphia, PA · On-site

$55 - $72.75/hr

Our Insurance Transformation practitioners serve as trusted advisors to our clients, combining strategic thinking with deep industry knowledge to solve complex business problems in a team-based ...

Deloitte

Guidewire Architect

Pittsburgh, PA · On-site

$59 - $76.75/hr

Our Insurance Transformation practitioners serve as trusted advisors to our clients, combining strategic thinking with deep industry knowledge to solve complex business problems in a team-based ...

Chubb

Claims Transformation Domain Lead

Philadelphia, PA · On-site

$180K - $275K/yr

The VP, Claims Transformation Domain Lead will spearhead the design and delivery of next-generation ... insurance, reinsurance, and life insurance to a diverse group of clients. The company is ...

Chubb

Claims Transformation Domain Lead

Philadelphia, PA · On-site

$180K - $275K/yr

The VP, Claims Transformation Domain Lead will spearhead the design and delivery of next-generation ... About Us Chubb is a world leader in insurance. With operations in 54 countries, Chubb provides ...

next page

Showing results 1-20

All JobsInsurance Transformation JobsInsurance Transformation Jobs in Pennsylvania

Insurance Transformation information

What is insurance transformation?

Insurance transformation refers to the process where insurance companies adopt new technologies, processes, and business models to improve efficiency, customer experience, and competitiveness. This often involves digitalizing operations, leveraging data analytics, and automating workflows to better meet the changing needs of customers and regulatory environments. The goal is to modernize legacy systems, streamline claims and underwriting, and create innovative insurance products. Successful transformation can help insurers stay relevant in a rapidly evolving industry and respond more quickly to market demands.

What are the key skills and qualifications needed to thrive in insurance transformation, and why are they important?

To thrive in Insurance Transformation, you need a solid understanding of insurance operations, digital transformation principles, and project management, often supported by a degree in business, IT, or related fields. Familiarity with core insurance platforms, data analytics tools, and certifications like PMP or Agile methodologies is highly valuable. Exceptional communication, change management, and stakeholder collaboration skills help drive adoption and manage organizational shifts. These capabilities are crucial for successfully leading modernization efforts and ensuring insurers remain competitive in a rapidly evolving industry.

What are some common challenges faced by professionals working in insurance transformation roles?

Professionals in Insurance Transformation often encounter challenges such as navigating legacy systems, managing resistance to change among staff, and aligning technology upgrades with regulatory requirements. These roles require strong project management and communication skills to successfully implement new digital solutions while ensuring minimal disruption to daily operations. Collaborating with cross-functional teams—including IT, compliance, and business units—is crucial for achieving seamless transitions and long-term success.

What is the difference between Insurance Transformation vs Insurance Underwriter?

AspectInsurance TransformationInsurance Underwriter
Primary RoleLeading initiatives to modernize and optimize insurance processes, systems, and business modelsAssessing risks and determining policy terms for individual insurance applications
Required SkillsProject management, change management, industry knowledge, technical skillsRisk assessment, underwriting expertise, industry regulations, decision-making
Work EnvironmentCross-functional teams, strategic planning, often in corporate or consulting settingsUnderwriting departments, insurance companies, client-facing roles
CertificationsTypically none specific; industry knowledge and project management certifications helpfulChartered Property Casualty Underwriter (CPCU), Fellow of the Insurance Institute of America (IIA)

Insurance Transformation focuses on modernizing insurance operations through strategic initiatives, while Insurance Underwriters evaluate individual risks to determine policy terms. Both roles require industry knowledge, but their responsibilities and work environments differ significantly.

What are popular job titles related to Insurance Transformation jobs in Pennsylvania?

For Insurance Transformation jobs in Pennsylvania, the most frequently searched job titles are:

What job categories do people searching Insurance Transformation jobs in Pennsylvania look for?

The top searched job categories for Insurance Transformation jobs in Pennsylvania are:

What cities in Pennsylvania are hiring for Insurance Transformation jobs?

Cities in Pennsylvania with the most Insurance Transformation job openings:

Insurance Transformation jobs near you
Infographic showing various Insurance Transformation job openings in Pennsylvania as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution.

Senior Director, Insurance Transformation (Project Management)

The Hagerty Group, LLC

Folsom, PA • On-site

Full-time

This job post has expired today. Applications are no longer accepted.

Hagerty rating

8.0

Company rating: 8.0 out of 10

Based on 14 frontline employees who took The Breakroom Quiz

171st of 315 rated insurance

Job description

Say hello to Hagerty
Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. We're proud to be the world's largest insurer of collectible and enthusiast vehicles and are home to the Hagerty Drivers Club, the world's largest car club. Our Marketplace business presents live and digital sales across the U.S. and Europe, we host a number of driving events and concours, and our award-winning automotive journalists produce the most popular car magazine globally, alongside internationally awarded videos. We're committed to Never Stop Driving. Ready to get in the driver's seat? Join us!
The Senior Director of Insurance Transformation is the senior execution leader responsible for driving predictable delivery of Hagerty's Apex insurance platform transformation. This role is designed for a hands-on project management professional with deep experience delivering large-scale core insurance system implementations (e.g., Duck Creek, Guidewire, Majesco).
What you'll do
Program Execution & Delivery Leadership
  • Own the integrated master schedule for Apex across multiple parallel workstreams (Policy, Billing, Claims, Distribution, Data, Integrations, Forms).
  • Build, maintain, and continuously refine the critical path and critical chain, identifying true constraints and protecting delivery buffers.
  • Actively manage cross-team dependencies, sequencing work to optimize end-to-end outcomes rather than local efficiency.
  • Force explicit trade-offs between scope, timing, and capacity, escalating decisions early with data-backed recommendations.
  • Re-forecast milestones and delivery dates based on actual execution reality, not static plans.

Project Management & Integration
  • Lead and integrate the work of multiple Project Managers responsible for bounded delivery slices (e.g., state readiness, capability releases).
  • Ensure project-level plans roll up coherently into the integrated program schedule.
  • Eliminate "late discovery" by enforcing readiness criteria before work begins (requirements, environments, data, dependencies).
  • Act as the single point of synthesis across business and IT delivery efforts.

Capacity, Risk & Constraint Management
  • Partner with IT APMO to align delivery plans with real engineering and vendor capacity.
  • Identify bottlenecks and systemic constraints early; re-sequence work proactively.
  • Actively manage delivery risk, buffer consumption, and emerging execution threats.
  • Ensure risks are surfaced as program-level decisions, not absorbed silently at the team level.

This might describe you
  • Proven experience delivering complex, cross-functional transformation initiatives, preferably in insurance or financial services.
  • Experience in multiple project/program delivery methods, Scrum, SAFe, etc.
  • Demonstrated hands-on experience with core insurance system implementations (Duck Creek).
  • Vendor management experience.
  • Proven expertise in:
    • Dependency mapping across parallel workstreams
    • Work sequencing under real constraints
    • Critical path and critical chain planning
    • Capacity and bottleneck management
    • Rolling schedule and delivery forecasting
  • Strong executive communication skills, including the ability to challenge optimistic assumptions constructively.
  • Advanced proficiency with project planning and tracking tools (e.g., ADO, Smartsheet, Lucid, similar).

Above and beyond
  • PMP Certification (Project Management Professional).
  • Experience working within a matrixed organization or enterprise PMO/TMO environment.
  • Background in systems modernization, insurance platform implementations, or large-scale operational transformation initiatives.
  • Familiarity with Agile, hybrid, or iterative delivery models in large transformations.
  • Background in insurance operations (underwriting, policy admin, billing, claims, distribution) strongly preferred.

Other things to note
  • This position is open to U.S. remote work. However, team members who reside within 20 miles of the Traverse City headquarters will follow a hybrid schedule, working from the office three days per week.
  • Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable. For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable.

If you reside in the following jurisdictions: Illinois, Colorado, California, District of Columbia, Hawaii, Maryland, Minnesota, Nevada, New York, or Jersey City, New Jersey, Cincinnati or Toledo, Ohio, Rhode Island, Washington, British Columbia, Canada please email recruiting@hagerty.com for compensation, comprehensive benefits and the perks that set us apart.
At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference. We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world.
#LI-Remote
EEO/AA
US Benefits Overview
Canada Benefits Overview
UK Benefits Overview
If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!

What Hagerty employees say

Pay

Benefits

Hours and flexibility

Workplace

Get the full story on Breakroom

Apply